72 Minutes With Mark Penn

Breaking down campaign strategy with the former Clinton Svengali turned Microsoft attack dog.

I have five or six key lessons from politics,” says Mark Penn, the veteran pollster and adviser to both Clintons, in his glass-lined capital office, “and one of them is that you’ve got to be explaining who you are, what makes you unique, and what sets you apart.” Penn, 59, is known for what insiders call “contrast,” the kind of slashing, negative advertisement that can dig a candidate out from a fifteen-point hole. As the chief strategist on Hillary Clinton’s 2008 race, he was the man behind the “3 a.m. phone call” ad that helped tank Obama in the March primaries. He’s also the guy who not so subtly brought up Obama’s past cocaine use in a televised interview and whose sideline as a consultant for a foreign government got him dropped in the home stretch of Hillary’s campaign. Not that Penn spends much time revisiting those memories. “The only thing I would like to have changed was the outcome,” he says.

His Beltway profile suffered, but his reputation as a pugilist apparently did not. In July 2012, he signed on full-time as a strategist for the faltering Microsoft. The mission was to shake up the company’s long-standing reluctance to push back publicly against its rivals, Apple and Google, who have been eating up market share. In July, a month before Microsoft announced that CEO Steve Ballmer was on the way out, the company reorganized, putting Penn in charge of advertising, in addition to his strategy portfolio, signaling that Microsoft intended to fight at last. “Let’s understand that competitive is in our bag now,” he says as he reclines in his office chair. “People like brands that stand up and say, ‘Hey, no, no, no—let me show you what we do here.’ ”

Penn’s thinning hair is mussed and his shirttail appears to be making an escape from the waistband of his suit pants. But his office is immaculate, one wall dominated by an enormous touchscreen, the others dotted with photos of him with Bill Clinton. It is also filled with metaphors of flight. “That is the Saturn V,” he says, gesturing to a large-scale model of the moon-shot rocket. His desk itself is a recycled airplane wing. “The theme is that we’re taking off,” he says. The floor-to-ceiling windows behind him overlook Washington’s K Street corridor. Microsoft’s government-affairs team works in a space several stories above, but this half of the building’s fifth floor is dedicated solely to Penn’s handpicked staff—a group known as “the SWAT team.”

That Microsoft should be in need of a heavily armed quick-reaction force, at least figuratively, says volumes about its change in tactics. Penn’s first major ad campaign is called “Scroogled,” which warns web surfers about Google’s data-tracking practices. Other ads go hard after Apple. In one TV spot, an iPad with a Siri-esque voice laments that in comparison to Surface, Microsoft’s entry into the tablet market, she is both less functional—“Oh, snap, you have a real keyboard, too?”—and more expensive. “Do you still think I’m pretty?” she asks forlornly at the end. Penn isn’t the first to bring contrast ads into the tech arena, of course. The Siri ads look like an updated version of Apple’s own notorious “I’m a Mac; I’m a PC” ads. It’s just new for Microsoft to do the fighting.

“I was going to show you ‘Girlfriend,’ ” Penn says as he roots around on the tablet in front of him, mumbling softly to himself. When he touches the play button, a winsome actress appears on the screen, standing in a bar. “Honestly, I wanted a phone with a better camera,” she says, before enumerating the megapixel-specific features of a phone made by Nokia, the handset-maker that Microsoft is in the process of acquiring. “So I went with a Windows Phone,” she says. “Maybe I just see things other people don’t.”

“You notice that it frames the choice that she’s making,” Penn tells me, still looking at the screen. “She is, very politely, going through her decision and drawing a contrast. But she’s also supplying the facts in considerable detail.” It’s not dissimilar—pop soundtrack aside—from the ads Penn created for Bill Clinton’s reelection campaign in 1996, telling voters the story of the four years they’d just lived through. The height of the form was a one-minute beauty called “America Back,” which combined audio of the president speaking in maudlin terms about values while onscreen titles listed his achievements in an unending list of Pennian phrases: “Welfare reform, work requirements … death penalty for drug kingpins … $1,500 tax credit …”

“President Clinton really is the master of this—he taught me that words matter,” he says. “And substance and detail matter.

“Politics and technology were the two things that I loved since I was a boy, pretty much,” he says as we walk down a sunlit row of SWAT-team desks outside his office. “I go back to when we had the first overnight polls with Ed Koch” for his race in 1977. “We did it on a microprocessor that I built from a kit.” During the Clinton years, Penn used polling to identify little slices of the electorate that the campaign should target, famously unearthing “soccer moms.” At Microsoft, he bases his decision-making on “really extensive, regular surveying” of consumers overlaid with sales data. The picture, he says, is encouraging. “You take this product,” Penn says of Surface. When it was introduced last year, “sales were not as strong. This year, we’re sold out.”

We’ve arrived at the heart of Penn’s operation, a war room fitted with an arc-shaped desk and oversize touchscreens for videoconferencing. At the moment, though, the screens are showing Joe Biden, who is holding an online town hall on immigration reform, using video questions from viewers via Skype, which Microsoft owns, and hosted by Bing, its search engine. “The vast majority of the American people support this!” Biden is saying. Penn looks on with interest. He has been careful this afternoon not to make any reference to ideas of professional redemption, but it’s clear that he’s eager to win again. In the past, the White House has partnered with Twitter and Google-owned YouTube for live-streaming. Today Microsoft is getting a turn. Penn claims he did not “personally” make the ask. Unspoken is the fact that Joe Biden isn’t his guy—and that Penn will never be an inner member of the Obama world. But, he says, “Let’s just say, now they have a choice.”